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Transformations of peroxide ozonolysis products of cyclic and acyclic natural olefins with different degrees of saturation by hydroxylamine and semicarbazide hydrochlorides were investigated.Ozonolytic cleavage of olefins is a convenient method of functionalizing compounds containing multiple bonds. Therefore, transformations of peroxide products of olefin ozonolysis are broadly used in preparative organic synthesis. They can be divided into two types, i.e., those occurring with retention of an oxidation level that is intermediate between a carbonyl and carboxylic acid (cleavage reaction) and with its transformation (reduction and oxidation reactions). In the middle of the twentieth century all these types of transformations of peroxide ozonolysis products were actively studied using a variety of reagents and thermal and photochemical degradation. However, in our opinion, N-containing organic compounds have seen limited use for these purposes and are represented in ozonolysis−reduction reactions by thiourea [1], tetracyanoethylene [2, 3], pyridine [4], tertiary amines [5], and amino-N-oxides [6]; in ozonolysis−cleavage reactions by triethylamine in combination with water [3] or acetic anhydride [7-9].The goal of our work was to study the reduction of peroxide ozonolysis products of cyclic and acyclic natural olefins with different levels of substitution by organic N-containing compounds of various nature in methanol and the isolation and identification of reduction products and subsequent transformations to N-and carboxyl-containing compounds that are promising for rational organic synthesis of α,ω-bifunctional synthons and compounds with potential pharmacological and biological activity.We studied di-[triglyceride of ricinic acid (1)]-and tri-[Δ 3 -carene (2) and (+)-α-pinene (3)]-substituted olefins using hydroxylamine and semicarbazide hydrochlorides as reagents.The use of hydroxylamine hydrochloride for transformation of peroxide products of olefin ozonolysis is limited to several examples. They were all carried out in methanol and resulted in the formation of aldehydes [10], an aldoxime [11,12], and an ester [13], depending on the nature of the substrates.Based on these examples, we proposed two probable schemes for forming an ester by treatment of peroxide ozonolysis products with hydroxylamine hydrochloride. The first pathway was aldehyde → aldoxime → nitrile → ester. An alternate pathway assuming dehydration of the methoxyhydroperoxide using an acid catalyst was also possible:

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Research from the last 20 years on the use of ozonolysis of cyclic and acyclic mono-and dienes and aromatic compounds in various steps of the total synthesis of insect pheromones and juvenoids was reviewed.

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